US1973647A - Process of synthetically producing ephedrin homologue and its salts - Google Patents
Process of synthetically producing ephedrin homologue and its salts Download PDFInfo
- Publication number
- US1973647A US1973647A US433816A US43381630A US1973647A US 1973647 A US1973647 A US 1973647A US 433816 A US433816 A US 433816A US 43381630 A US43381630 A US 43381630A US 1973647 A US1973647 A US 1973647A
- Authority
- US
- United States
- Prior art keywords
- ephedrin
- homologue
- salts
- solution
- nitro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 title description 11
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 title description 9
- 229960002179 ephedrine Drugs 0.000 title description 9
- 238000000034 method Methods 0.000 title description 8
- 150000003839 salts Chemical class 0.000 title description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FXYHSMPIVUZFLS-UHFFFAOYSA-N 1-nitro-1-phenylethanol Chemical compound [O-][N+](=O)C(O)(C)C1=CC=CC=C1 FXYHSMPIVUZFLS-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- FEJLPMVSVDSKHJ-UHFFFAOYSA-N 3-methyl-1-nitrobutane Chemical compound CC(C)CC[N+]([O-])=O FEJLPMVSVDSKHJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000005569 Iron sulphate Substances 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000031018 biological processes and functions Effects 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- -1 nitro- Chemical class 0.000 description 2
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 1
- QPBPOOLKXPFDTD-UHFFFAOYSA-N 1-nitro-1-phenylpropan-1-ol Chemical compound CCC(O)([N+]([O-])=O)C1=CC=CC=C1 QPBPOOLKXPFDTD-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 239000001120 potassium sulphate Substances 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
Definitions
- This invention relates to the process of synthetically producing ephedrin homologue and its salts, "resembling in its chemical and biological action, ephedrin which is obtainable by reducing, in the presence or absence of formaldehyde, nitro-alcohol obtained by the condensation of benzaldehyde with nitro-ethane in the presence of alkali and the object of the invention is to produce a substitute for natural or synthetic ephedrin, economically.
- the ether is distilled away from the ethereal solution which leaves phenyl-nitroethanol, the yield of which is from 75% to 80% of the thereotical.
- the alcoholic solution is made alkaline by adding potassium carbonate to it, then the upper layer is separated from the lower layer,
- EXAMPLE II A mixture of one molecule of phenyl-nitroethanol described in the Example I and one molecule of formaldehyde is reduced by means of excess zinc dust, and 30% acetic acid, and the zinc is then removed by flowing hydrogen sulphide therein, and a small quantity of neutral substance and acetic acid is dissolved and passed into ether.
- hydrochloric acid is added to the aque- 60 ous solution, which is then evaporated under diminished pressure, a chloride remains which crystallizes out from solution in a small quantity of an absolute alcohol. After treating this chloride in the same manner as described in the preceding I example, a base shown in the title of this example having a melting point of 77 C. is obtained.
- EXAMPLE III 1 -phcnyl-2-amino-4-methyZ-pentan-1 -ol OH; CuHs-CH(OH)OH(NH2)OHzCH 170 grams of light-colored, oily, crude phenyl-nitro-methyl-pentanol are obtained by treating in the same manner as above described, a condensation product formed by shaking 106 grams of benzaldehyde, 117 grams of nitro-isopentane and 100 c. c. of 40% potassium carbonate solution for 80 about 4 weeks.
- This condensation product is reduced by means of alcohol, iron filings, and 30% sulphuric acid as described above, then the iron sulphate thus formed is precipitated by alcohol, filtered oh, and 35 then the residue obtained by distilling off alcohol from the solute is made strongly alkaline by adding caustic soda thereto, shaken with ether, and then the ether is removed by distillation.
- this residue is evaporated under diminished pressure, a tabular or flat needle-like chloride is obtained, by neutralizing a free base having a boiling point of from 170 to 172 C. (18 mm.) by alcoholic hydrochloric acid, and then adding ether.
- a base shown in the title of this example is obtained by treating the above mentioned chloride in the same manner as the Example 1.
- the U. S. Patent No. 1,356,877 relates to the process of producing methyl-mydriatin or artificial ephedrin by reducing phenyl-nitro-propanol obtained from benzaldehyde and nitro-ethane by the action of a solution of weak alkaline organic or inorganic substance, such as alkali metal carbonates, bicarbonates, phosphates, or pyridine etc., in the presence of formaldehyde solution, 05 with acetic acid or iron dust.
- weak alkaline organic or inorganic substance such as alkali metal carbonates, bicarbonates, phosphates, or pyridine etc.
- This invention employs the above patent, as this invention is an improvement of the process of said patent, and is a process of producing ephedrin homologue and its salts in which nitro- 1'10 2.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Sept. 11, 1934 UNITED STATES? PROCESS OF SYNTHETICALLY PRODUCING EPHEDRIN HOMOLOGUE AND ITS SALTS Chogi Nagai, deceased, late of Shibuya-Machi,
Toyotama-Gun,
Tokyo, Japan, by Alexander Nagai, heir, Berlin, Germany No Drawing. Application March 6, 1930, Serial No. 433,816. In Japan August 6, 1929 2 Claims.
This invention relates to the process of synthetically producing ephedrin homologue and its salts, "resembling in its chemical and biological action, ephedrin which is obtainable by reducing, in the presence or absence of formaldehyde, nitro-alcohol obtained by the condensation of benzaldehyde with nitro-ethane in the presence of alkali and the object of the invention is to produce a substitute for natural or synthetic ephedrin, economically.
The following data are given by way of examples according to this invention.
EXAMPLE I 1 -phenyZ-2-amino-ethan-1 -0Z CsHs-CH (OH) CH2NH2.
A condensation product formed by agitating 106 grams of benzaldehyde and 61 grams of nitro- ;methane with c. c. of potassium bicarbonate solution for several hours, is dissolved in ether and is shaken with sodium bisulphite solution, and is then shaken with an alkali metal carbonate solution. The ether is distilled away from the ethereal solution which leaves phenyl-nitroethanol, the yield of which is from 75% to 80% of the thereotical.
An alcoholic solution of 167 grams of phenylnitroethanol, formed by the above mentioned process, dissolved in 800 c. c. of alcohol, is reduced by adding 1600 grams of 25% sulphuric acid and 240 grams of iron filings alternately, and the iron sulphate thus formed is then precipitated by means of alcohol. The alcoholic solution is made alkaline by adding potassium carbonate to it, then the upper layer is separated from the lower layer,
and is neutralized by adding sulphuric acid, thus precipitating potassium sulphate which is filtered off. When the alcohol in the filtrate is distilled away, and the residue is crystallized from alcohol by recrystallization, a sulphate of rhombic tabular form is obtained. When to this aqueous solution, caustic soda is added and is shaken with ether, and the ether is then distilled away from this ethereal solution, a base shown in the title of this example having a melting point of about 40 C. remains.
EXAMPLE II A mixture of one molecule of phenyl-nitroethanol described in the Example I and one molecule of formaldehyde is reduced by means of excess zinc dust, and 30% acetic acid, and the zinc is then removed by flowing hydrogen sulphide therein, and a small quantity of neutral substance and acetic acid is dissolved and passed into ether. When the two layers are separated from each other, and hydrochloric acid is added to the aque- 60 ous solution, which is then evaporated under diminished pressure, a chloride remains which crystallizes out from solution in a small quantity of an absolute alcohol. After treating this chloride in the same manner as described in the preceding I example, a base shown in the title of this example having a melting point of 77 C. is obtained.
EXAMPLE III 1 -phcnyl-2-amino-4-methyZ-pentan-1 -ol OH; CuHs-CH(OH)OH(NH2)OHzCH 170 grams of light-colored, oily, crude phenyl-nitro-methyl-pentanol are obtained by treating in the same manner as above described, a condensation product formed by shaking 106 grams of benzaldehyde, 117 grams of nitro-isopentane and 100 c. c. of 40% potassium carbonate solution for 80 about 4 weeks.
This condensation product is reduced by means of alcohol, iron filings, and 30% sulphuric acid as described above, then the iron sulphate thus formed is precipitated by alcohol, filtered oh, and 35 then the residue obtained by distilling off alcohol from the solute is made strongly alkaline by adding caustic soda thereto, shaken with ether, and then the ether is removed by distillation. When this residue is evaporated under diminished pressure, a tabular or flat needle-like chloride is obtained, by neutralizing a free base having a boiling point of from 170 to 172 C. (18 mm.) by alcoholic hydrochloric acid, and then adding ether. A base shown in the title of this example is obtained by treating the above mentioned chloride in the same manner as the Example 1.
The U. S. Patent No. 1,356,877 relates to the process of producing methyl-mydriatin or artificial ephedrin by reducing phenyl-nitro-propanol obtained from benzaldehyde and nitro-ethane by the action of a solution of weak alkaline organic or inorganic substance, such as alkali metal carbonates, bicarbonates, phosphates, or pyridine etc., in the presence of formaldehyde solution, 05 with acetic acid or iron dust.
This invention employs the above patent, as this invention is an improvement of the process of said patent, and is a process of producing ephedrin homologue and its salts in which nitro- 1'10 2. The method of synthetically producing ephedrine homologue, resembling ephedrine in its chemical and biological action by reducing, in the use of formaldehyde, the nitro-alcohol obtained by the condensation of benzaldehyde with a nitroparafline selected from the group consisting of nitromethane and nitro-iso-pentane, in the presence of alkali metal carbonate.
ALEX. NAGAI, Heir to the Late Chogi Nagai.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1973647X | 1929-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1973647A true US1973647A (en) | 1934-09-11 |
Family
ID=16373256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US433816A Expired - Lifetime US1973647A (en) | 1929-08-06 | 1930-03-06 | Process of synthetically producing ephedrin homologue and its salts |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1973647A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2474792A (en) * | 1946-02-25 | 1949-06-28 | Commercial Solvents Corp | Polyamino alcohols and method for preparing them |
| US2586512A (en) * | 1948-09-15 | 1952-02-19 | Searle & Co | Cyclohexyl-amino-alcohols |
| US4327228A (en) * | 1979-06-14 | 1982-04-27 | Beecham Group Limited | 3-Nitro-1-phenyl-1-(m-chlorophenyl)-propan-2-ol. |
| US5750802A (en) * | 1995-06-07 | 1998-05-12 | Amvac Chemical Corporation | (1R*, 2S)-1-phenyl-2-nitroalcohols and method for producing same |
| EP0960876A1 (en) * | 1997-07-31 | 1999-12-01 | Amvac Chemical Corporation | (1R*, 2S*)-1-Phenyl-2-nitroalcohols and method for producing same |
-
1930
- 1930-03-06 US US433816A patent/US1973647A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2474792A (en) * | 1946-02-25 | 1949-06-28 | Commercial Solvents Corp | Polyamino alcohols and method for preparing them |
| US2586512A (en) * | 1948-09-15 | 1952-02-19 | Searle & Co | Cyclohexyl-amino-alcohols |
| US4327228A (en) * | 1979-06-14 | 1982-04-27 | Beecham Group Limited | 3-Nitro-1-phenyl-1-(m-chlorophenyl)-propan-2-ol. |
| US5750802A (en) * | 1995-06-07 | 1998-05-12 | Amvac Chemical Corporation | (1R*, 2S)-1-phenyl-2-nitroalcohols and method for producing same |
| EP0960876A1 (en) * | 1997-07-31 | 1999-12-01 | Amvac Chemical Corporation | (1R*, 2S*)-1-Phenyl-2-nitroalcohols and method for producing same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US1973647A (en) | Process of synthetically producing ephedrin homologue and its salts | |
| DE1938513B1 (en) | Process for the preparation of D-threo-1-p-methylsulfonyl-phenyl-2-dichloroacetamido-propane-1,3-diol | |
| DE1493757A1 (en) | Process for the production of mixed carbonic acid esters | |
| US1867274A (en) | Resolution of ephedrine and its homologues and of mandelic acid, and certain intermediates | |
| US1356877A (en) | Mydriatic and process of making same | |
| DE1166201B (en) | Pressureless process for the preparation of hydantoins which are mono- or disubstituted in the 5-position | |
| Wilson et al. | 302. The optically active diphenylhydroxyethylamines and iso heydrobenzoins. Part VII. The 1: 2-cyclo-hexanediols and related compounds | |
| US2011454A (en) | Process of synthetically producing ephedrin homologue and its salts | |
| US1888794A (en) | Process of preparing salts of the chloroethane sulphonic acid | |
| US545099A (en) | Albrecht schmidt | |
| DE604406C (en) | ||
| US1306710A (en) | Hiroshi nomtjra | |
| Dox et al. | The Reaction between sym-Dichloro-dimethyl Ether and Ethyl Malonate. | |
| US1816248A (en) | Manufacture of aromatic hydroxy aldehydes | |
| DE614462C (en) | Process for the preparation of basic substituted enol compounds | |
| DE82816C (en) | ||
| Skinner | DEAMINIZATION OF METHYL DEXTRO-CIS-3-AMINO-1, 2, 2-TRIMETHYL CYCLOPENTANOATE | |
| DE2936416C2 (en) | ||
| DE1938513C (en) | Process for the preparation of D threo 1 p methylsulfonyl phenyl 2 dichloracetami do propane 1,3 diol | |
| Price et al. | CXVIII.—The preparation of disulphides. Part V. Diethyl esters of α-dithiodibutyric, α-dithiodi iso-butyric, and α-dithiodi iso valeric acids | |
| SU175956A1 (en) | ||
| DE567923C (en) | Process for the preparation of aminoquinolines | |
| PL22157B1 (en) | A method for producing alkali-substituted enol compounds. | |
| AT72452B (en) | Process for the preparation of salts of menthol and borneol sulfuric acids. | |
| US496113A (en) | Constantin fahlberg |